none 10.3987/COM-02-9612 CLOCKSS Archive CLOCKSS Archive 5187 36504518 73640 20090309112757 10.13030 2024-06-24T20:34:44Z 2009-03-09T04:01:45Z 3 HETEROCYCLES HETEROCYCLES 0385-5414 HTCYAM 2002 57 12 Yoshinori Tominaga Yasuhiro Shigemitsu Shun-ichi Hirayama 2002 2227 COM-02-9612 10.3987/COM-02-9612 20090309112757 https://triggered.stanford.clockss.org/ServeContent?doi=10.3987%2Fcom-02-9612 https://triggered.edinburgh.clockss.org/ServeContent?doi=10.3987%2Fcom-02-9612 a) A. T. Petera and H. S. Freeman, “Colour Chemistry: The Design and Synthesis of Organic Dyes and Pigments,” Advances in Colour Chemistry Series, Elsevier Applied Science, New York, 1991; b) D. R. Waring and G. Halls, “The Chemistry and Application of Dyes,” Plenum Press, New York, 1991; 10.1021/cr00014a003 c) J. Fabian, H. Nakazumi, and M. Matsuoka, Chem. Rev., 1992, 92, 1197; d) S. G. R. Guinot, J. D. Hepworth, and M. Wainwright, J. Chem. Soc., Perkin Trans. 2, 1998, 2972; d) Y. Matsuda, K. Katou, H. Matsumoto, S. Ide, K. Takahashi, K. Torisu, K. Furuno, and S. Maeda, Yakugaku Zasshi, 1992, 112, 42 and references cited therein. 10.1021/ja001047n 2. C. Kanony, B. Akerman, and E. M. Tuite, J. Am. Chem. Soc., 2001, 123, 7985. 10.2116/bunsekikagaku.45.111 a) M. Mizoguchi, M. Ishiyama, M. Shiga, and K. Sasamoto, Bunseki Kagaku, 1996, 45, 111; 10.1248/cpb.41.620 b) M. Mizoguchi, M. Shiga, and K. Sasamoto, Chem. Pharm. Bull., 1993, 41, 620; c) K. L. Cheng, K. Ueno, and T. Imamura, “Handbook of Organic Analytical Reagents,” CRC Press, Inc., Boca Raton, p. 267, 1982. 10.3987/COM-97-S12 a) Y. Tominaga, K. Komiya, S. Itonaga, N. Yoshioka, S. Kataoka, K. Sasaki, and T. Hirota, Heterocycles, 1997, 46, 41; 10.3987/COM-01-9260 b) Y. Tominaga, S. Itonaga, T. Kouno, and Y. Shigemitsu, Heterocycles, 2001, 55, 1447. 10.1248/cpb.21.2770 5. Y. Tominaga, R.Natsuki, Y. Matsuda, and G. Kobayashi, Chem. Pharm. Bull., 1973, 21, 2770. 6. Though the stereochemistry of the products has not been decided, the structures shown in the figure have been estimated from the NMR spectra and the result of calculation by MOPAC. 7. 4: Dark violet leaflets, mp 312-315 °C (DMF). 1H-NMR (DMSO-d6) δ: 3.29 (6H, s, 2xNMe), 3.81 (6H, s, 2 x OMe), 3.86 (6H, s, 2 x OMe), 6.30 (2H, s, C=H), 7.14 (2H, dd, J=7.4, 8.2 Hz, 7, 7’-H), 7.35 (2H, dd, J=7.4, 8.0 Hz, 8, 8’-H), 7.66 (2H, d, J=8.0 Hz, 9, 9’-H), 7.76 (2H, d, J=8.2 Hz, 6, 6’-H). MS m/z: 656 (M+). 8. 5: Red leaflets, mp 231-234 °C (MeOH). 1H-NMR (CDCl3 + CF3COOD) δ: 3.17 (3H, s, Me), 4.13 (3H, s, NMe), 4.14 (3H, s, OMe), (3H, s, OMe), 7.77 (1H, t, J=8.2 Hz, 7-H), 7.89 (1H, d, J=8.2 Hz, 8-H), 7.96 (1H, t, J=8.2 Hz, 9-H), 8.45 (1H, d, J=8.2 Hz, 6-H). 9. 6: Greenish yellow needles, mp 275-278°C (MeOH). 1H-NMR (CDCl3) δ: 3.74 (3H, s. NMe), 3.91 (3H, s, OMe), 3.97 (3H, s, OMe), 5.03 (1H, s, C=H), 5.76 (1H, s, C=H), 7.19-7.37 (3H, m, 6, 7, 8-H), 7.90 (1H, d, J=7.4 Hz, 9-H). MS m/z: 329 (M+, 100). 10. 8a: Black crystals, mp 230 °C (decomp) (MeOH). Ms m/z: 462 (M+). 8b: balck crystals, mp 240 °C (decomp), Ms m/z : 489 (M+). 8c: black crystals, mp 230-240 °C (decomp) (MeOH), FAB MS:487 (M++1). 11. 10: Dark violet leaflets, mp 216-218 °C (MeOH), 1H-NMR (CDCl3) δ: 3.88 (3H, s, NMe), 3.97 (3H, s, OMe), 4.04 (3H, s, OMe), 6.30 (1H, d, J=12.4 Hz, C=H), 7.22-7.44 (3H, m, 7, 8, 9-H), 7.74 (1H, d, J=8.2 Hz, 6-H), 8.24 (1H, d, J=12.4 Hz, C=H). 12. 11: Black crystals, mp 210-232 °C (CH2Cl2), 1H-NMR (CDCl3) δ: 3.77 (3H, s, NMe), 4.03 (3H, s, OMe), 4.07 (3H, s, OMe), 6.40 (1H, s, C=H), 7.09-7.61 (4H, m, 6, 7, 8, 9-H), MS m/z: 430 (M+). 13. 12: Black crystals, mp 230-232 °C (MeOH), 1H-NMR (CDCl3) δ: 3.14 (3H, s, NMe), 4.02 (3H, s, NMe), 4.03 (3H, s, OMe), 4.09 (3H, s, OMe), 6.64 (1H, s, C=H), 6.70 (1H, d, J=8.00 Hz, 6-H), 7.27-7.65 (3H, m, 7, 8, 9-H), MS:m/z 464 (M+).